Benzyl Chloride → 4-(Chloromethyl)benzene-1-sulfonyl chloride

HRID 1901233Notes

Reaction equation

HRID 1901233 reaction equation
[Cl:1][S:2]([OH:5])(=O)=[O:3].[CH2:6]([Cl:13])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>>[Cl:13][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([S:2]([Cl:1])(=[O:5])=[O:3])=[CH:9][CH:8]=1

Participants

3

Reactant 2

HCID 7503Benzyl ChlorideHCID 24638Chlorosulfonic acid

Product 1

HCID 225013994-(Chloromethyl)benzene-1-sulfonyl chloride

Procedure

To a 250 mL flask, fitted with addition funnel, reflux condenser and thermometer, is placed 50 g (0.43 mole) of chlorosulfonic acid. Benzyl chloride, (18 g, 0.14 mole) is added to the reaction mixture, slowly, with continuous stirring, over a period of two hours. The temperature of the reaction is kept near room temperature using a water bath. After the addition is complete, the stirring is continued for at least one hour. After analysis by thin layer chromatography shows that the reaction is complete, the reaction mixture is poured into 150 g of crushed ice. The solid is collected and washed with cold water several times. The crude product is further purified by recrystallization. The product is characterized using 1H NMR spectroscopy.

Workup

  1. customTo a 250 mL flask, fitted with addition funnel
  2. temperaturereflux condenser
  3. customis kept near room temperature
  4. additionAfter the addition
  5. waitthe stirring is continued for at least one hour
  6. customThe solid is collected
  7. washwashed with cold water several times
  8. customThe crude product is further purified by recrystallization

Sources & evidence

ORD record
ord-24248eaafa434dfba3e8c13d58f2054d
Source dataset
uspto-grants-1996_11
Patent number
US05576424

Reaction notes

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